A young Portsmouth fan strikes a defiant note during a recent game at Fratton Park. Photograph: James Benwell/Action Images

Portsmouth's administrator, Trevor Birch, evidently feels his gloomy message from shell-shocked Fratton Park has not been fully digested, so he decided to spell it out, alarmingly. Two years after their last existence-threatening crisis, Pompey, formed in 1898, really could go bust this time. In administration for the second time in two years following the arrest for alleged bank fraud of their most recent owner, the Russian Vladimir Antonov, Portsmouth do not have enough money to see them through until the end of the season.

The portions of remaining parachute payments following the club's relegation from the Premier League, which occurred as recently as the season before last, are already spoken for; £2.2m is owed to Alexandre "Sacha" Gaydamak, a French-Israeli owner, who oversaw and for a time bankrolled massive overspending on players' transfers and wages. That brought Pompey the 2008 FA Cup, under Harry Redknapp, but then, when Gaydamak's money ran out, resulted in the first hideous administration and the club's collapse into crisis.

Birch warned: "Portsmouth could be the first big club to fail to fulfil its fixtures and go into liquidation." That sparked a flurry of calls to the Football League's HQ about what happens to the Championship table if a 114-year-old football club ceases to exist, to which the answer is that its results for the season are wiped out. The Football League does not believe that will happen because it expects a buyer will come forward, a prospect the Pompey Supporters Trust is also talking up – its chairman, Ashley Brown, pointing to the long tradition and "loyal, passionate fans."

Birch pointed to the legacy – or, to be precise, the lack of one – bequeathed by the years in which millions were paid in wages to Sol Campbell, Jermain Defoe, Peter Crouch, Lassana Diarra and other players the club could not afford without Gaydamak's financial backing. Fratton Park, for all the talk of grand redevelopments, has barely been touched and still seats 20,000. Pompey have no training ground and Birch said the school on whose fields the first team trains, King Edward VI in Southampton, is warning of eviction because the club cannot commit to a lease. Nor is there a youth academy – Birch said the young players turn up at Fratton Park, then are driven by minibus to sundry playing fields.

"There is no infrastructure," Birch said, "but, counting this administration and the last one, there is more than £100m of debt run up. How has that happened?"

The answer is the dire and dismal consequence of placing the existence of historic and passionately followed football clubs into the commitment of "owners" whose resources are uncertain. Gaydamak was only 29 when he bought Portsmouth from Milan Mandaric for around £50m, always insisting he had made his money himself, and was not using funds from his father, Arcady, who in October 2009 was prosecuted in Israel over money laundering – a charge which was reportedly dropped last month when he pleaded guilty to a lesser offence. Sacha told Portsmouth's then chief executive, Peter Storrie, in 2009 that he could no longer fund the club, and the club went on to become the first Premier League side to fall into administration.

Before that, Gaydamak passed Pompey on to another owner, the Dubai-based property entrepreneur, Sulaiman al-Fahim who soon moved it on to Ali al-Faraj, a Saudi Arabian businessman who never appeared at Fratton Park. A loan was taken out with Portpin, a company owned by the Hong Kong-based businessman Balram Chainrai, who became the next owner, taking the club out of administration.

Chainrai then sold in June last year to Antonov, who was introduced and represented by the serial football takeover banker, Keith Harris. Chainrai retained a secured debenture for a debt of £17m on the club itself; he also has one on Antonov's Convers Sports Initiative, which went into administration when it failed to pay him an instalment and the Russian was arrested. Antonov denies "asset stripping" at a Lithuanian bank.

Thus, the 2008 FA Cup winners, who finished eighth in the billionaires' Premier League that same year under Redknapp, find themselves insolvent again, 10 points deducted in the Championship, and fighting to avoid relegation while the administrator warns they could go out of existence altogether. And with £2.2m still owed to Gaydamak, the last owner but five.